923604-57-3

Basic information

• Product Name: siMeprevir interMediate
• Synonyms: siMeprevir interMediate;(2R,3aR,10Z,11aS,12aR,14aR)-2,3,3a,4,5,6,7,8,9,11a,12,13,14,14a-Tetradecahydro-2-[[7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-4-quinolinyl]oxy]-5-methyl-4,14-dioxocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a(1H)-carboxylic acid ethyl ester;Simeprevir cyclized intermediate
• CAS NO: 923604-57-3
• Molecular Formula: C37H46N4O6S
• Molecular Weight: 674.84934
• EINECS: -0
• Mol File: 923604-57-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• Vapor Pressure: 0-0Pa at 20-25℃
• PKA: 13.24±0.60(Predicted)
• CAS DataBase Reference: siMeprevir interMediate(CAS DataBase Reference)
• NIST Chemistry Reference: siMeprevir interMediate(923604-57-3)
• EPA Substance Registry System: siMeprevir interMediate(923604-57-3)

Safety Data

• Hazardous Substances Data: 923604-57-3(Hazardous Substances Data)

Usage

General Description

SiMeprevir is an antiviral drug used to treat hepatitis C. The chemical siMeprevir intermediate is a key component in the synthesis of siMeprevir. It serves as an essential building block in the manufacturing process, allowing for the production of siMeprevir in a controlled and efficient manner. The chemical undergoes various reactions and transformations during the synthesis process, ultimately leading to the formation of siMeprevir. As an intermediate, this chemical plays a crucial role in the pharmaceutical production of siMeprevir, contributing to the drug's overall efficacy and safety in treating hepatitis C.

Upstream product

• 862174-60-5 (1R,4R,5R)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid 
• 1703-61-3 rac-4-oxocyclopentane-1,2-dicarboxylic acid 
• 1042695-84-0 methyl (1R,2R,4R)-2-[5-hexen-1-yl-(methyl)carbamoyl]-4-hydroxycyclopentanecarboxylate 
• 862174-98-9 (1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide 
• 1431935-31-7 C₄₁H₄₅F₇N₄O₇S 
• 1431935-30-6 C₃₉H₄₅ClF₂N₄O₇S 
• 1431935-27-1 C₄₁H₄₉F₃N₄O₇S 
• 1431935-29-3 C₃₉H₄₅F₃N₄O₇S 
• 923604-56-2 ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate 

Downstream Products

• 923604-59-5 simeprevir 

Relevant articles and documents

Ring-Closing Metathesis on Commercial Scale: Synthesis of HCV Protease Inhibitor Simeprevir

The key macrocyclization step in the synthesis of simeprevir, a hepatitis C virus (HCV) antiviral drug, was studied. N-Boc substitution on the diene precursor changes the site of insertion of the metathesis catalyst and, consequently, the kinetic model of the ring closing metathesis (RCM), enabling a further increase in the macrocyclization efficiency under simulated high dilution (SHD) conditions. NMR of the inserted species of both first and second generation RCM catalysts are reported and discussed.

HCV INHIBITING MACROCYCLIC PHOSPHONATES AND AMIDOPHOSPHATES

Inhibitors of HCV replication of Formula (I) the /V-oxides, salts, and stcreochcmically isomeric forms thereof; pharmaceutical compositions containing compounds (1) and processes for preparin compounds (I). The side chain R2 is an amidophosphate or a phosphonate group and X, R1, R3, E and n are as defined in the application.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.